Amine-catalyzed Michael reactions of an aminoaldehyde derivative to nitroolefins

被引：31
作者：
Albertshofer, Klaus
Thayumanavan, Rajeswari
Utsumi, Naoto
Tanaka, Fujie
Barbas, Carlos F., III
机构：
[1] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA
[2] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
[3] Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA
来源：
TETRAHEDRON LETTERS | 2007年 / 48卷 / 04期
关键词：
Michael reaction; aminoaldehyde; nitroolefin; asymmetric reactions; amine; enamine;
D O I：
10.1016/j.tetlet.2006.11.096
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Catalytic enantioselective Michael addition reactions of alpha-amino functionalized aldehydes to nitroolefins have been developed. The Michael product was obtained in tip to 98% ee, but the enantiomeric purity of the Michael product was decreased during isolation of the product. (c) 2006 Elsevier Ltd. All rights reserved.
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收藏
页码：693 / 696
页数：4
相关论文
共 35 条
[1]   Diamine-catalyzed asymmetric Michael additions of aldehydes and ketones to nitrostyrene [J].
Alexakis, A ;
Andrey, O .
ORGANIC LETTERS, 2002, 4 (21) :3611-3614
[2]   The use of N-alkyl-2,2′-bipyrrolidine derivatives as organocatalysts for the asymmetric Michael addition of ketones and aldehydes to nitroolefins [J].
Andrey, O ;
Alexakis, A ;
Tomassini, A ;
Bernardinelli, G .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (9-10) :1147-1168
[3]   Catalytic direct asymmetric Michael reactions: Addition of unmodified ketone and aldehyde donors to alkylidene malonates and nitro olefins [J].
Betancort, JM ;
Sakthivel, K ;
Thayumanavan, R ;
Tanaka, F ;
Barbas, CF .
SYNTHESIS-STUTTGART, 2004, (09) :1509-1521
[4]   Catalytic direct asymmetric Michael reactions: Taming naked aldehyde donors [J].
Betancort, JM ;
Barbas, CF .
ORGANIC LETTERS, 2001, 3 (23) :3737-3740
[5]   Catalytic enantioselective direct Michael additions of ketones to alkylidene malonates [J].
Betancort, JM ;
Sakthivel, K ;
Thayumanavan, R ;
Barbas, CF .
TETRAHEDRON LETTERS, 2001, 42 (27) :4441-4444
[6]   Pyrrolidine-thiourea as a bifunctional organocatalyst: Highly enantioselective Michael addition of cyclohexanone to nitroolefins [J].
Cao, Chun-Li ;
Ye, Meng-Chun ;
Sun, Xiu-Li ;
Tang, Yong .
ORGANIC LETTERS, 2006, 8 (14) :2901-2904
[7]   5-Pyrrolidin-2-yltetrazole as an asymmetric organocatalyst for the addition of ketones to nitro-olefins [J].
Cobb, AJA ;
Longbottom, DA ;
Shaw, DM ;
Ley, SV .
CHEMICAL COMMUNICATIONS, 2004, (16) :1808-1809
[8]  
Enders D., 2002, SYNLETT, P26
[9]   Ni(II)-bis[(R,R)-N,N′-dibenzylcyclohexane-1,2-diamine]Br2 catalyzed enantioselective Michael additions of 1,3-dicarbonyl compounds to conjugated nitroalkenes [J].
Evans, DA ;
Seidel, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (28) :9958-9959
[10]   Diphenylprolinol silyl ethers as efficient organocatalysts for the asymmetric Michael reaction of aldehydes and nitroalkenes [J].
Hayashi, Y ;
Gotoh, H ;
Hayashi, T ;
Shoji, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (27) :4212-4215
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